I am a carry everything gal, too, but I don't do multiple bags to match my outfits nor Vera Bradley. I am pretty conservative and more of a "classic" dresser. I carry a brown leather Fossil bag. Not small. Not big. It has compartments and zippers inside and the outside has two small slots on either end. EVERYTHING in my purse has "a place". But I cannot stick extraneous things in it (like hubby's sunglasses, lol). It has a removable shoulder strap and regular hand hold handles.
I am very particular when I shop for a purse and do not switch them out. I wear them out, then buy a new one. ;) It is SUCH a pain to change everything out from one purse to another.
Cough strips, lipsticks, compact, pens, pencils, wallet, coupon wallet, advil, neosporin, nail clippers, change, keys, phone, emory board, discount cards, chapstick, dental floss, etc....... It's just too much to try to move it all, and I don't want to leave ANY of it behind! lol